New Abietane and Kaurane Type Diterpenoids from the Stems of Tripterygium regelii

Int J Mol Sci. 2017 Jan 13;18(1):147. doi: 10.3390/ijms18010147.

Abstract

Eleven new abietane type (111), and one new kaurane (12), diterpenes, together with eleven known compounds (13-23), were isolated and identified from the stems of Tripterygium regelii, which has been used as a traditional folk Chinese medicine for the treatment of rheumatoid arthritis in China. The structures of new compounds were characterized by means of the interpretation of high-resolution electrospray ionization mass spectrometry (HRESIMS), extensive nuclear magnetic resonance (NMR) spectroscopic data and comparisons of their experimental CD spectra with calculated electronic circular dichroism (ECD) spectra. Compound 1 is the first abietane type diterpene with an 18→1 lactone ring. Compound 19 was isolated from the plants of the Tripterygium genus for the first time, and compounds 14-17 were isolated from T. regelii for the first time. Triregelin I (9) showed significant cytotoxicity against A2780 and HepG2 with IC50 values of 5.88 and 11.74 µM, respectively. It was found that this compound was inactive against MCF-7 cells. The discovery of these twelve new diterpenes not only provided information on chemical substances of T. regelii, but also contributed to the chemical diversity of natural terpenoids.

Keywords: Tripterygium regelii; cytotoxicity; diterpenoids.

MeSH terms

  • Abietanes / chemistry
  • Abietanes / isolation & purification*
  • Abietanes / pharmacology
  • Carbon-13 Magnetic Resonance Spectroscopy
  • Cell Death / drug effects
  • Cell Line, Tumor
  • Circular Dichroism
  • Diterpenes, Kaurane / chemistry
  • Diterpenes, Kaurane / isolation & purification*
  • Diterpenes, Kaurane / pharmacology
  • Humans
  • Plant Stems / chemistry*
  • Proton Magnetic Resonance Spectroscopy
  • Tripterygium / chemistry*

Substances

  • Abietanes
  • Diterpenes, Kaurane